U.S. patent number 10,328,003 [Application Number 15/735,755] was granted by the patent office on 2019-06-25 for solubilizing agents for active or functional organic compounds.
This patent grant is currently assigned to ISP INVESTMENTS LLC. The grantee listed for this patent is ISP INVESTMENTS LLC. Invention is credited to Hani M. Fares, Anna A. Gripp, Ilya Makarovsky, Osama M. Musa, Krishnamurthy Nacharaju, Donald I. Prettypaul, Michael A. Tallon.
![](/patent/grant/10328003/US10328003-20190625-C00001.png)
![](/patent/grant/10328003/US10328003-20190625-C00002.png)
![](/patent/grant/10328003/US10328003-20190625-C00003.png)
![](/patent/grant/10328003/US10328003-20190625-C00004.png)
![](/patent/grant/10328003/US10328003-20190625-C00005.png)
![](/patent/grant/10328003/US10328003-20190625-C00006.png)
![](/patent/grant/10328003/US10328003-20190625-C00007.png)
![](/patent/grant/10328003/US10328003-20190625-C00008.png)
![](/patent/grant/10328003/US10328003-20190625-C00009.png)
![](/patent/grant/10328003/US10328003-20190625-C00010.png)
![](/patent/grant/10328003/US10328003-20190625-C00011.png)
View All Diagrams
United States Patent |
10,328,003 |
Makarovsky , et al. |
June 25, 2019 |
Solubilizing agents for active or functional organic compounds
Abstract
A photo protective topical composition, comprising: (i) at least
one functional active; and (ii) at least one solubilizing compound
having the structure of Formula I: ##STR00001## wherein R is
C.sub.5-C.sub.10 cycloalkyl or linear or branched alkylcycloalkyl,
wherein the ring size is C.sub.5-C.sub.7; R.sub.1, R.sub.2, and
R.sub.3 are each independently selected from the group consisting
of H, and linear or branched C.sub.1-C.sub.4 alkyl, provided that
at least two of R.sub.1, R.sub.2, R.sub.3 are H; wherein the
solubilizing compound is present in an amount effective to
solubilize said functional active. Also disclosed is a method for
treating skin, lips, nails, hair, ears, eyelashes, eyebrows and/or
scalp with an effective amount of composition.
Inventors: |
Makarovsky; Ilya (Fair Lawn,
NJ), Tallon; Michael A. (Aberdeen, NJ), Fares; Hani
M. (Somerset, NJ), Prettypaul; Donald I. (Englewood,
NJ), Nacharaju; Krishnamurthy (Hilliard, OH), Gripp; Anna
A. (Whippany, NJ), Musa; Osama M. (Bedminster, NJ) |
Applicant: |
Name |
City |
State |
Country |
Type |
ISP INVESTMENTS LLC |
Wilmington |
DE |
US |
|
|
Assignee: |
ISP INVESTMENTS LLC
(Wilmington, DE)
|
Family
ID: |
57504411 |
Appl.
No.: |
15/735,755 |
Filed: |
June 10, 2016 |
PCT
Filed: |
June 10, 2016 |
PCT No.: |
PCT/US2016/036938 |
371(c)(1),(2),(4) Date: |
December 12, 2017 |
PCT
Pub. No.: |
WO2016/201260 |
PCT
Pub. Date: |
December 15, 2016 |
Prior Publication Data
|
|
|
|
Document
Identifier |
Publication Date |
|
US 20180168970 A1 |
Jun 21, 2018 |
|
Related U.S. Patent Documents
|
|
|
|
|
|
|
Application
Number |
Filing Date |
Patent Number |
Issue Date |
|
|
62174995 |
Jun 12, 2015 |
|
|
|
|
Current U.S.
Class: |
1/1 |
Current CPC
Class: |
C07C
69/76 (20130101); A61K 8/4966 (20130101); A61P
17/16 (20180101); A61Q 17/04 (20130101); A61K
8/37 (20130101); A61K 2800/49 (20130101); A61K
2800/262 (20130101); C07C 2601/14 (20170501); C07C
2601/08 (20170501) |
Current International
Class: |
A61K
8/37 (20060101); A61K 8/49 (20060101); A61P
17/16 (20060101); A61Q 17/04 (20060101); C07C
69/76 (20060101) |
References Cited
[Referenced By]
U.S. Patent Documents
Foreign Patent Documents
Other References
International Search Report, PCT/US2016/036938 published on Dec.
15, 2016. cited by applicant.
|
Primary Examiner: Sasan; Aradhana
Attorney, Agent or Firm: Davis; William J. Chen; Shaorong
Tietcheu; Nathalie
Claims
What is claimed is:
1. A photo protective topical composition, comprising: i. at least
one functional active; and ii. at least one solubilizing compound
having the formula I, ##STR00013## wherein R is C.sub.5-C.sub.10
cycloalkyl or linear or branched alkylcycloalkyl, wherein the ring
size is C.sub.5-C.sub.7; R.sub.1, R.sub.2, and R.sub.3 are each
independently selected from the group consisting of H, and linear
or branched C.sub.1-C.sub.4 alkyl, provided that at least two of
R.sub.1, R.sub.2, R.sub.3 are H; wherein said compound is present
in an amount effective to solubilize said functional active.
2. The composition according to claim 1, wherein said composition
is visibly transparent and free of odor.
3. The composition according to claim 1, wherein said solubilizing
compound is selected from the group consisting of cyclohexyl
2-toluate, cyclohexyl 3-toluate, cyclohexyl 4-toluate,
cyclohexylmethanol 3-toluate, cyclopentyl 3-toluate,
cycloheptyl-m-toluate and combinations thereof.
4. The composition according to claim 3, wherein said solubilizing
compound is selected from cyclohexyl 3-toluate, cyclohexyl
4-toluate and combinations thereof.
5. The composition according to claim 1, wherein said solubilizing
compound is present in an amount of about 0.1% wt./wt. to about 70%
wt./wt. of the total photo protective topical composition.
6. The composition according to claim 1, wherein said functional
active is present in an amount of about 1% wt./wt. to about 70%
wt./wt. of the total photo protective topical composition.
7. The composition according to claim 1, wherein said photo
protective topical composition is a personal care, cosmetic care,
pharmaceutical or nutraceutical composition.
8. The composition according to claim 1, wherein said functional
active is a personal care active, cosmetic care active,
pharmaceutical active or nutraceutical active.
9. The composition according to claim 8, wherein said personal care
active is a sunscreen active containing Ultra Violet (UV) A and/or
UVB active agent.
10. The composition according to claim 8, wherein said personal
care composition capable of demonstrating increased retention of UV
absorption after exposure to UV radiation.
11. The composition according to claim 9, wherein said sunscreen
active is selected from the group consisting of octyl salicylate;
p-aminobenzoic acid, PEG-25PABA, Ethylhexyl dimethyl PABA, pentyl
dimethyl PABA, octyl dimethyl PABA, amyl dimethyl PABA,
benzophenone-1, benzophenone-2, benzophenone-3, benzophenone-4,
benzophenone-5, benzophenone-6, benzophenone-8, benzophenone-9,
2-(2H-benzotriazole-2-yl)-4,6-di-tert-pentylphenol,
ethyl-2-cyano-3,3-diphenyl acrylate, homo menthyl salicylate,
his-ethyl hexyloxyphenol methoxy phenyl triazine (bemotrizinol),
methyl-(1,2,2,6,6-pentamethyl-4-piperidyl)-sebacate,
2-(2H-benzotriazole-2-yl)-4-methylphenol, diethylhexyl butamido
triazone, 4,6-bis-(octylthiomethyl)-o-cresol,
Poly(4-hydroxy-2,2,6,6-tetramethyl-1-piperidine
ethanol-alt-1,4-butanedioic acid), red petroleum, octocrylene,
isoamyl-p-methoxycinnamate, drometrizole, drometrizole trisiloxane,
bisoctrizole,
2,4-di-tert-butyl-6-(5-chloro-2H-benzotriazole-2-yl)-phenol,
2-hydroxy-4-octyloxy benzophenone, diisopropyl methylcinnamate,
2-(1,1-dimethylethyl)-6-[[3-(1,1-demethylethyl)-2-hydroxy-5-methylphenyl]-
methyl-4-methylphenyl-acrylate, menthyl anthranilate, butyl methoxy
dibenzoyl methane, 2-ethoxyethyl p-methoxycinnamate, benzylidene
camphor sulfonic acid,
dimethoxyphenyl-[1-(3,4)]-4,4-dimethyl1,3-pentanedione,
N,N'-hexane-1,6-diylbis-[3-(3,5-di-tert-butyl-4-hydroxyphenyl-propionamid-
e)], pentaerythritol tetrakis
[3-(3,5-di-tert-butyl-4-hydroxyphenyl) propionate],
2,6-di-tert-butyl-4-[4,6-bis(octylthio)-1,3,5-triazin-2-ylamino]
phenol,
2-(2H-benzotriazole-2-yl)-4,6-bis(1-methyl-1-phenylethyl)phenol,
trolamine salicylate, diethylanolamine p-methoxycinnamate,
polysilicone-15, 4-methylbenzylidene camphor, n-phenyl-benzenamine,
reaction products of 2,4,4-trimethylpentene,
(2-ethylhexyl)-2-cyano-3,3-diphenylacrylate, digalloyl trioleate,
polyacrylamido methylbenzylidene camphor, glyceryl ethylhexanoate
dimethoxycinnamate,
1,3-bis-[(2'-cyano-3',3'-diphenylacryloyl)oxy]-2,2-bis-{[(2'-cyano-bis-(2-
,2,6,6-tetramethyl-4-piperidyl)-sebacate,
1,3,5-tris(3,5-di-tert-butyl-4-hydroxybenzyl)-1,3,5-triazine-2,4,6(1H,3H,
5H)-trione, hexamethylendiamine, ethyl-4-bis(hydroxypropyl)
aminobenzoate,
6-tert-butyl-2-(5-chloro-2H-benzotriazole-2-yl)-4-methyl phenol,
3,3',3'',5,5',5''-hexa-tert-butyl-.alpha.-.alpha.'-.alpha.''-(mes-
itylene-2,4,6-triyl) tri-p-cresol, ethylhexyl dimethoxybenzylidene
dioxoimidazoline propionate,
N,N'-bisformyl-N,N'-bis-(2,2,6,6-tetramethyl-4-piperidinyl),
3-benzylidene camphor, terephthalylidene dicamphor sulfonic acid,
camphor benzalkonium methosulfate, bisdisulizole disodium,
etocrylene, ferulic acid,
2-(2H-benzotriazole-2-yl)-4-(1,1,3,3-tetramethylbutyl)-phenol,
4,6-bis(dodecylthiomethyl)-o-cresol, .beta.-2-glucopyranoxy propyl
hydroxy benzophenone, phenylbenzimidazole sulfonic acid,
diethylamine hydroxy benzoyl hexylbenzoate,
3',3'-diphenylacryloyl)oxy]methyl}-propane, ethylhexyl
p-methoxycinnamate, avobenzone, camphor benzalkonium methosulfate,
phenylbenzimidazole sulfonic acid, terephthalidene dicamphor
sulfonic acid, benzylidene camphor sulfonic acid,
polyacrylamidomethyl benzylidene camphor, ethylhexyl
methoxycinnamate, ethylhexyl triazone, diethylhexyl butamido
triazone, 4-methylbenzylidene camphor, 3-benzylidene camphor,
methylene-bis-benztriazolyl tetramethylbutylphenol, disodium phenyl
dibenzimidazole tetrasulfonate, bisethylhexyloxyphenol
methoxyphenol triazine, polysilicone-15, 2,4,6-tris(Diisobutyl
4-aminobenzalmalonate)-s-triazine, titanium dioxide, zinc oxide,
micronized or unmicronized mixtures thereof.
12. The composition according to claim 9, wherein said sunscreen
active is present in an amount of about 1% wt./wt. to about 70%
wt./wt. of the total composition.
13. The composition according to claim 11, wherein said sunscreen
active is bisethylhexyloxy phenol methoxyphenol triazine.
14. The composition according to claim 1, wherein said composition
further comprises a mineral photo protective agent present in an
amount of about 0.01% wt./wt. to about 70% wt./wt. of the total
composition.
15. The composition according to claim 14, wherein said photo
protective agent is treated or untreated metal oxide pigments or
nanopigments selected from the group consisting of treated or
untreated titanium oxide, zinc oxide, iron oxide, zirconium oxide,
cerium oxide and mixtures thereof.
16. The composition according to claim 1, wherein said composition
further comprises at least one agent for artificially tanning
and/or browning the skin selected from dihydroxy acetone, isatin,
alloxan, ninhydrin, glyceraldehyde, mesotartaric aldehyde,
glutaraldehyde, erythrulose alone or in combination thereof.
17. The composition according to claim 1, wherein said composition
further comprises at least one adjuvant or additive selected from
secondary polymers for improving water-resistance, UV active
solubilizers, oils, waxes, solvents, emulsifiers, preservatives,
antioxidants, vitamins, insect repellants, dyes, pigments,
humectants, fillers, thickeners, film formers, stabilizers,
buffers, spreading agents, pearlizing agents, electrolytes, acids,
bases, fatty substances, ionic thickeners, non-ionic thickeners,
hydrophilic thickeners, lipophilic thickeners, softeners,
opacifiers, emollients, silicones, antifoaming agents, fragrances,
anionic surfactants, cationic surfactants, nonionic surfactants,
zwitterionic surfactants, amphoteric surfactants, active agents,
propellants, acidifying or basifying agents, antioxidants,
.alpha.-hydroxy acids, moisturizing agents, anti-inflammatory,
colorants, pharmaceutically or dermatologically or cosmetically
acceptable excipients, and combinations thereof.
18. The composition according to claim 1, wherein said photo
protective topical composition is formulated into an oil-in-water
emulsion, a water-in-oil emulsion, an oil-water-oil emulsion, a
water-oil-water emulsion, a water-in-silicone emulsion, an oily
solution, a lipid fusion, a hydro-alcoholic gel, an anhydrous
formulation, an anhydrous spray, an anhydrous gel, an anhydrous dry
gel, an aqueous gel, a gel cream SPF 20, a SPF 30 cream, an
alcoholic solution, a hydro-alcoholic solution, a milk, a lotion, a
powder, a stick, a roll-on, a mist, a wipe, a wax, a mousse, an
aerosol, a balm, a patch, a pomade, a pump spray, a solution, a
towelette, a paste, a powder or a spray.
19. A method for cosmetically treating or caring for the skin,
lips, nails, hair, ears, eyelashes, eyebrows and/or scalp
comprising topically applying an effective amount of a photo
protective topical composition comprising (i) at least one
functional active; and (ii) at least one solubilizing compound
having the formula I: ##STR00014## wherein R is C.sub.5-C.sub.10
cycloalkyl or linear or branched alkylcycloalkyl, wherein the ring
size is C.sub.5-C.sub.7; R.sub.1, R.sub.2, and R.sub.3 are each
independently selected from the group consisting of H, and linear
or branched C.sub.1-C.sub.4 alkyl, provided that at least two of
R.sub.1, R.sub.2, R.sub.3 are H; wherein said solubilizing compound
is present in an amount effective to solubilize said functional
active.
20. A method for photo protecting the exposed and/or unexposed
skin, nails, hair, lips, ears, eyebrows, eyelashes, and/or scalp,
against the damaging effects of UV-irradiation comprising topically
applying an effective amount of a cosmetic/dermatological
composition comprising: (i) at least one active, and (ii) at least
one solubilizing compound having the formula I ##STR00015## wherein
R is C.sub.5-C.sub.10 cycloalkyl or linear or branched
alkylcycloalkyl, wherein the ring size is C.sub.5-C.sub.7; R.sub.1,
R.sub.2, and R.sub.3 are each independently selected from the group
consisting of H, and linear or branched C.sub.1-C.sub.4 alkyl,
provided that at least two of R.sub.1, R.sub.2, R.sub.3 are H;
wherein said solubilizing compound is present in an amount
effective to solubilize said functional active.
21. A photo protective topical sunscreen composition for the
UV-photo protection of human skin and/or hair comprising: a) about
1% wt./wt. to about 70% wt./wt. of at least one active sunscreen
agent of claim 11; b) about 0.1% wt./wt. to about 50% wt./wt. of at
least one solubilizing compound selected from cyclohexyl 3-toluate,
cyclohexyl 4-toluate or combination thereof; and c) about 1%
wt./wt. to about 80% wt./wt. of at least one topically applicable
cosmetically or dermatologically acceptable carrier.
22. The composition according to claim 21, wherein said composition
further comprises at least one adjuvant or additive selected from
secondary polymers for improving water-resistance, UV active
solubilizers, oils, waxes, solvents, emulsifiers, preservatives,
vitamins, insect repellants, dyes, pigments, humectants, fillers,
film formers, stabilizers, buffers, spreading agents, pearlizing
agents, electrolytes, acids, bases, fatty substances, organic
solvents, ionic thickeners, non-ionic thickeners, hydrophilic
thickeners, lipophilic thickeners, softeners, opacifiers,
emollients, silicones, antifoaming agents, fragrances, anionic
surfactants, cationic surfactants, nonionic surfactants,
zwitterionic surfactants, amphoteric surfactants, active agents,
fillers, propellants, acidifying or basifying agents, antioxidants,
.alpha.-hydroxy acids, moisturizing agents, anti-inflammatory
agents, colorants, pharmaceutically or dermatologically or
cosmetically acceptable excipients, and combinations thereof.
Description
FIELD OF INVENTION
This application relates to a topical composition, and more
particularly, to a photo protective composition comprising (i) at
least one functional active; and (ii) at least one solubilizing
compound, wherein, the composition is visibly transparent, free of
odor and freeze-thaw stable.
BACKGROUND OF THE INVENTION
The skin's appearance and health is continuously affected by
various factors including, for example, humidity, UV light,
cosmetics, aging, diseases, stress, cigarette smoking, and eating
habits, each of which can result in various skin changes.
Additionally, certain changes appear on the skin that is
characteristic of aging or exposure to sun, many of which are
reflected, in particular, by a change in the skin's structure. The
main clinical signs of aging of the skin are, in particular, the
appearance of fine lines and deep wrinkles, each of which can
increase with age. Wrinkles can be caused by both the chronological
aging of the skin, and photo aging of skin due to exposure of the
skin to sunlight, UV-radiation, and other forms of actinic
radiation.
It is well-known that sunlight radiation ranging from 290 to 400 nm
is detrimental to organic materials, including human skin, and
particularly radiation with wavelengths between 290 and 320 nm,
so-called UV-B region is responsible for the occurrence of erythema
and sunburns, whose severity depends on exposure length.
Furthermore, it has been ascertained that radiation between 320 and
400 nm, so-called UV-A, which is responsible for skin tanning, can
cause alterations and important damages in skin, especially in the
case of sensitive skin, or in the case of continuous exposure to
the radiation. It has been shown that UV-A radiation, besides
causing damage to elastin and collagen, the consequence of which is
skin ageing, can also be the cause of a number of phototoxic and
photo allergic reactions. Moreover, the harmful action of UV-B can
also be enhanced by the presence of UV-A.
Many commercial products, e.g., personal care, sunscreen,
pharmaceutical, agricultural and industrial compositions which
contain active or functional compounds are available. These active
or functional compounds often require solubilization in the form of
a solution, emulsion or dispersion, in aqueous or non-aqueous form.
For example, sunscreen formulations containing aromatic compounds
such as avobenzone (Escalol.RTM.517) and/or benzophenone-3
(Escalol.RTM.567) active UVA/UVB absorbing ingredients require a
solubilization to prevent crystallization. Several such
solubilizers are known, e.g., ethyl benzoate and a
C.sub.12-C.sub.15 alkyl benzoate (Finosolve TN; Witconol APM
manufactured and marketed by Witco). However, the former compound
is a strong irritant, and the latter is only a poor solvent for
avobenzone and benzophenone-3.
U.S. Pat. Nos. 7,166,275 and 7,691,363 assigned to ISP Investments
Inc. disclose compositions of an active or functional organic
compound solubilized in a phenyl ethyl ester which is an aryl
carboxylic ester of 2-phenylethyl alcohol. The phenyl ethyl ester
can be 2-phenylethyl benzoate, toluate or phthalate. The active or
functional organic compound can be a solid organic compound, e.g.,
a personal care, cosmetic, sunscreen, pharmaceutical, agricultural
or industrial compound. Preferred actives include active sunscreen
ingredients, e.g., UVA and/or UVB sunscreens such as avobenzone
and/or benzophenone-3. X-Tend.TM. 226, marketed by Ashland
Specialty Ingredients, is the ester of 2-phenylethyl alcohol and
benzoic acid. It has a high solubilizing capacity for solid organic
sunscreen materials such as oxybenzone and avobenzone and has
achieved widespread commercial acceptance. It exhibits excellent
skin feel and also increases the critical wavelength and the
UVA/UVB ratio of some formulations. It can also be used to enhance
shine in hair sprays, shine sprays, or styling creams. It has
colorless to light yellow liquid with faint odor of roses.
U.S. Pat. No. 7,785,573 assigned to ISP Investments Inc. discloses
active or functional organic compounds solubilized by an ester of
an aryl alcohol, e.g., phenethyl, benzyl or substituted benzyl
alcohol, and an alkyl or cycloalkyl carboxylic acid, or by a
carbonate of the aryl alcohol and an alkyl or cycloalkyl carbonic
acid.
U.S. Pat. No. 7,364,721 assigned to L'Oreal, discloses a cosmetic
composition including an active or functional organic compound,
which is solubilized by a safe and effective organic solvent such
as an aryl carboxylic ester of 2-phenylethyl alcohol, e.g.
2-phenylethyl benzoate, 2-phenylethyl toluate or di-2-phenylethyl
phthalate.
Despite the solutions proposed by the aforementioned patents and
other approaches described in the published literature, there still
exists a need for an effective cosmetic or dermatological
composition to reduce skin damage by exposure to UV radiation.
Thus it is desired to provide improved cosmetic or dermatological
compositions having better solubilizing compounds that are capable
of solubilizing functional or organic compounds employed therein,
particularly at low temperatures, and at the same time having
greater regulatory acceptability and consumer acceptability such as
reduced irritation or hypoallergic, odorless (free of pungent odor)
and/or colorless that causes inconvenience to users.
Accordingly, the primary objective of the present application is to
provide a photo protective composition capable of eliminating or
reducing undesired properties such as instability, irritation,
allergy, pungent odor, color, and other related issues.
SUMMARY OF THE INVENTION
In one aspect, the present application provides a photo protective,
topical composition comprising (i) at least one functional active;
and (ii) at least one solubilizing compound, having the formula
I:
##STR00002## wherein, R is C.sub.5-C.sub.10 cycloalkyl or linear or
branched alkylcycloalkyl, wherein the ring size is C.sub.5-C.sub.7;
R.sub.1, R.sub.2, and R.sub.3 are each independently selected from
the group consisting of H, and linear or branched C.sub.1-C.sub.4
alkyl, provided that at least two of R.sub.1, R.sub.2, R.sub.3 are
H; wherein said solubilizing compound is present in an amount
effective to solubilize said functional active.
In another aspect, the present application provides a solubilizing
compound (or agent) selected from the group consisting of
cyclohexyl 2-toluate, cyclohexyl 3-toluate, cyclohexyl 4-toluate,
cyclohexylmethanol 3-toluate, cyclopentyl 3-toluate,
cycloheptyl-3-toluate and combinations thereof present in an amount
of about 0.1% wt./wt. to about 70% wt./wt., preferably 0.1% wt./wt.
to about 50% wt./wt. of the total photo protective topical
composition.
In another aspect, the present application provides a photo
protective topical composition formulated into an oil-in-water
emulsion, a water-in-oil emulsion, an oil-water-oil emulsion, a
water-oil-water emulsion, a water-in-silicone emulsion, an oily
solution, a lipid fusion, a hydro-alcoholic gel, an anhydrous
formulation, an anhydrous spray, an anhydrous gel, an anhydrous dry
gel, an aqueous gel, a gel cream SPF 20, a SPF 30 cream, an
alcoholic solution, a hydro-alcoholic solution, a milk, a lotion, a
powder, a stick, a roll-on, a mist, a wipe, a wax, a mousse, an
aerosol, a balm, a patch, a pomade, a pump spray, a solution, a
towelette, paste, powder or a spray.
In still another aspect, the present application provides a method
for cosmetically treating or caring for the skin, lips, nails,
hair, ears, eyelashes, eyebrows and/or scalp comprising topically
applying thereon, an effective amount of the photo protective
topical composition of the present application.
In yet another aspect, the present application provides a method
for photo protecting the exposed and/or unexposed skin, nails,
hair, lips, ears, eyebrows, eyelashes, and/or scalp, against the
damaging effects of ultra violet (UV) irradiation comprising
topically applying thereon, an effective amount of the
cosmetic/dermatological composition of the present application.
In yet another aspect, the present application provides photo
protective topical sunscreen compositions for the UV protection of
human skin and/or hair comprising: (a) about 1% wt./wt. to about
70% wt./wt. of at least one active sunscreen agent; (b) about 0.1%
wt./wt. to about 50% wt./wt. of at least one solubilizing compound
selected from cyclohexyl 3-toluate, cyclohexyl 4-toluate or a
combination thereof; and (c) about 1% wt./wt. to about 80% wt./wt.
of at least one topically applicable, cosmetically or
dermatologically acceptable carrier.
BRIEF DESCRIPTION OF THE FIGURES
Further embodiments of the present invention can be understood with
reference to the appended figures.
FIG. 1 illustrates consumer odor evaluations for C12-15 alkyl
benzoate prior art and inventions.
FIG. 2 illustrates solubility of sunscreens in cyclohexyl toluate
of the invention and phenethyl benzoate at 25.degree. C.
FIG. 3 illustrates solubility of sunscreen agents in cyclohexyl
toluate and C12-15 alkyl benzoate at 25.degree. C.
FIG. 4 illustrates solubility of sunscreen agents in cyclohexyl
toluate and various esters.
FIG. 5 illustrates solubility of sunscreen agents in cyclohexyl
toluate and various esters.
FIG. 6 illustrates solubility comparison in Cyclohexyl Toluate and
C12-15 Alkyl Benzoate.
DETAILED DESCRIPTION OF THE INVENTION
While this specification concludes with claims particularly
pointing out and distinctly claiming that which is regarded as the
invention, it is anticipated that the invention can be more readily
understood through reading the following detailed description of
the invention and study of the included examples.
Unless otherwise defined herein, technical terms used in connection
with the disclosed and/or claimed inventive concept(s) shall have
the meanings that are commonly understood by those of ordinary
skill in the art. Further, unless otherwise required by context,
singular terms shall include pluralities and plural terms shall
include the singular.
All patents, published patent applications, and non-patent
publications referenced in any portion of this application are
herein expressly incorporated by reference in their entirety to the
same extent as if each individual patent or publication was
specifically and individually indicated to be incorporated by
reference.
As utilized in accordance with the disclosure, the following terms,
unless otherwise indicated, shall be understood to have the
following meanings.
The use of the word "a" or "an" when used in conjunction with the
term "comprising" mean "one," but it is also consistent with the
meaning of "one or more," "at least one," and "one or more than
one." The use of the term "or" is used to mean "and/or" unless
explicitly indicated to refer to alternatives only if the
alternatives are mutually exclusive, although the disclosure
supports a definition that refers to only alternatives and
"and/or."
All percentages, ratio, and proportions used herein are based on a
weight basis unless other specified.
As used herein, the words "comprising" (and any form of comprising,
such as "comprise" and "comprises"), "having" (and any form of
having, such as "have" and "has"), "including" (and any form of
including, such as "includes" and "include") or "containing" (and
any form of containing, such as "contains" and "contain") are
inclusive or open-ended and do not exclude additional, un recited
elements or method steps. The term "or combinations thereof" as
used herein refers to all permutations and combinations of the
listed items preceding the term. For example, "A, B, C, or
combinations thereof" is intended to include at least one of: A, B,
C, AB, AC, BC, or ABC and, if order is important in a particular
context, also BA, CA, CB, CBA, BCA, ACB, BAC, or CAB. Continuing
with this example, expressly included are combinations that contain
repeats of one or more item or term, such as BB, AAA, MB, BBC,
AAABCCCC, CBBAAA, CABABB, and so forth. The skilled artisan will
understand that typically there is no limit on the number of items
or terms in any combination, unless otherwise apparent from the
context.
The terms "preferred," "preferably", and variants thereof, refer to
embodiments of the invention that afford certain benefits, under
certain circumstances. However, other embodiments are also
preferred, under the same or other circumstances. Furthermore, the
recitation of one or more preferred embodiments does not imply that
other embodiments are not useful and is not intended to exclude
other embodiments from the scope of the invention.
References herein to "one embodiment" or "one aspect" or "one
version" or "one objective" of the application include one or more
such embodiment, aspect, version or objective, unless the context
clearly dictates otherwise.
The term "each independently selected from the group consisting of"
means when a group appears more than once in a structure, that
group can be selected independently each time it appears.
The term "alkyl" refers to a functionalized or unfunctionalized
monovalent straight-chain or branched-chain C.sub.1-C.sub.60 group
optionally having one or more heteroatoms. Particularly, an alkyl
is a C.sub.1-C.sub.45 group and more particularly, a
C.sub.1-C.sub.30 group. As used herein, the term alkyl refers to
C.sub.1-C.sub.4 group.
The term "branched" refers to any non-linear molecular structure.
The term includes both branched and hyper-branched structures.
The term "cosmetically acceptable ingredient" means any
ingredient/compound or mixture of ingredients/compounds or
compositions that are typically employed to produce other desirable
effects in personal care compositions.
The term "cosmetic/dermatological composition" as used herein is
intended to describe compositions for topical application to human
skin, including leave-on and wash-off products.
The terms "effective amount" and "effective use level" refer to a
sufficient amount of functional active or solubilizing agent
employed to provide desired performance attributes, stability,
efficacy, product aesthetics, and the like.
The term "hypoallergic" should be construed in a broad sense as
compound with reduced irritation and which doesn't sensitize the
skin or hair after topical application.
The term "free of odor" should be construed in a broad sense as
property of a substance that does not have any characteristic odor
or smell.
The term "freeze-thaw stable" as used herein refers to a kind of
stability test, wherein the sample under test is subjected to low
temperature as low as 0.degree. C. and then thawing the sample to
temperatures as high as 95.degree. C. This test describes the
ability of the product to remain stable under varied temperature
conditions.
The term, "functional active" as used herein refers to, e.g.,
chemically-active, pharmaceutically-active, or nutraceutically
active ions, molecules, complexes or polymers. It includes a
personal care, cosmetic, pharmaceutical, and nutraceutical active
compounds. Preferably, the functional active is a sunscreen
containing UVA and/or UVB active organic or a mineral photo
protective agent that is water-soluble or lipo soluble or insoluble
in cosmetic solvents commonly employed.
The terms "personal care composition" and "cosmetics" refer to
compositions intend for use on or in the human body, such as skin,
sun, hair, oral, cosmetic, eyebrows, eyelashes, and preservative
compositions, including those to alter the color and appearance of
the skin and hair.
The term "pharmaceutical composition" refers to any composition
comprising at least one pharmaceutically active ingredient, as well
as any product which results, directly or indirectly, from
combination, complexation, or aggregation of any two or more of the
ingredients, from dissociation of one or more of the ingredients,
or from other types of reactions or interactions of one or more of
the ingredients.
The term "pharmaceutical active" should be construed in a broad
sense as including any active ingredient considered to have a
therapeutic effect when delivered to a subject in need thereof and
further being regulated by drug authorities like CDER, EMEA, TAG,
etc. Pharmaceutically active ingredients can act systemically upon
oral consumption, or locally such as when present in the buccal
cavity, on the skin, etc. They can also be delivered across the
skin as in transdermal drug delivery systems.
The term "photo protective composition" includes cosmetic
compositions, personal care, pharmaceutical compositions and/or
nutraceutical compositions.
The term "photo protective" as used herein refers to the ability of
a functional active, preferably sunscreen active, to maintain its
integrity when exposed to sunlight when combined with the
cycloalkyl toluate based compound. A photo protective composition
generally has an SPF (sunscreen protection factor) of at least 6,
for example, and preferably at least 30, 45, 60 or 100. The SPF is
duly defined in "A new substrate to measure sunscreen protection
factors throughout the ultraviolet spectrum", J. Soc. Cosmet.
Chem., 40, 127-133, 1989 which is hereby incorporated by reference
in its entirety.
The term "photostable" as used herein refers to the ability of a
molecule to remain intact with irradiation.
The term "skin" as used herein includes the skin on the face, neck,
chest, back, abdomen, arms, hands, legs, feet, and scalp.
The term "SPF" as used herein refers to sun protection factor
(SPF)--defined as the dose of UVR required to produce 1 minimal
erythema dose (MED) on protected skin after the application of 2
mg/cm.sup.2 of product divided by the UVR required to produce 1 MED
on unprotected skin.
The term "sun care composition" refers to any composition intended
for use on the human body for protection from harmful or
undesirable radiation from sun rays.
The personal care industry requires improved cosmetic and
dermatological compositions, particularly those comprising
sunscreen or sun care actives. One of the biggest technological
challenges for sunscreen compositions is to effectively and
completely solubilize the functional active which often is
lipophilic and at the same time provide protection against harmful
UV radiations. The present application provides an effective means
of meeting the aforementioned unmet need.
What is described herein is a photo protective, topical composition
comprising: at least one functional active and at least one
cycloalkyl toluate based solubilizing compound, wherein, said
solubilizing compound is present in an amount effective to
solubilize said functional active. Further, the photo protective
topical composition is visibly transparent, free of odor,
hypoallergic, and free-thaw stable.
In accordance with the present invention, there is provided a photo
protective, topical composition comprising: (i) at least one
functional active; and (ii) at least one solubilizing compound
having the formula I:
##STR00003## wherein R is a C.sub.5-C.sub.10 cycloalkyl or a linear
or branched alkylcycloalkyl, wherein the ring size is
C.sub.5-C.sub.7; R.sub.1, R.sub.2 and R.sub.3 are H or a linear or
branched C.sub.1-C.sub.4 alkyl, provided that at least two of
R.sub.1, R.sub.2 and R.sub.3 are H; and wherein said solubilizing
compound is present in an amount effective to solubilize said
functional active.
Accordingly, "an effective amount" is the amount of at least one
solubilizing compound (or agent) required to solubilize at least
one functional active. The solubilizing compound of the present
application is present in an effective amount of from about 0.1%
wt./wt. to 70% wt./wt. of the total composition. Other non-limiting
ranges for solubilizing compound include 0.1% to 1%, 1% to 5%, 5%
to 10%, 10% to 15%, 15% to 20%, 20% to 25%, 25% to 30%, 30% to 50%
or 50% to 70%. However, the preferred range of solubilizing
compound employed to solubilize at least one functional active is
in the range of from about 5% wt./wt. to 10% wt./wt. of the total
composition.
In one preferred embodiment, the present application provides at
least one solubilizing compound (or agent) to solubilize the
functional actives, and wherein, the solubilizing compound belongs
to a group of cycloalkyl toluates. Non-limiting yet preferred
solubilizing compounds can be selected from the group consisting of
cyclohexyl 2-toluate, cyclohexyl 3-toluate, cyclohexyl 4-toluate,
cyclohexylmethanol 3-toluate, cyclopentyl 3-toluate, and
cycloheptyl-m-toluate, alone or in combinations thereof. The
representative structures of these non-limiting compounds would
include:
##STR00004##
According to another preferred and non-limiting embodiment, the
composition of present application includes combinations or
mixtures of Cyclohexyl-meta-toluate (Cyclohexyl-3-toluate) and
Cyclohexyl-para-toluate (Cyclohexyl-4-toluate) in a ratio of from
about 70:30 to about 5:95, preferably from about 10 to about 90.
This combination advantageously simplifies the formulation systems
as it does not necessitate any heating or homogenization prior to
use, and therefore, it is freeze-thaw stable.
In another specific and non-limiting embodiment, the present
application provides photo protective, topical composition, wherein
said composition is a personal care composition, cosmetic care
composition, dermatological care composition, pharmaceutical
composition, or nutraceutical care composition. Preferably, the
composition is personal care composition.
Non-limiting examples of personal care compositions include: a sun
care composition, face care composition, lip care composition, eye
care composition, skin care composition, after-sun care
composition, body care composition, nail care composition,
anti-aging composition, insect repellant, oral care composition,
deodorant composition, hair care composition, conditioning
composition, color cosmetic composition, color-protection
composition, self-tanning composition, and foot care composition.
In another non-limiting embodiment, the personal care composition
is a sun care composition, and more particularly, the sun care
composition is a highly effective photo stable and photo protective
composition.
In another non-limiting embodiment, the present application
provides a sun care composition formulated, for example into
products for application to the lips, hair, face, cheeks, neck,
area around the eyes, full hands, and body area. Additionally,
self-tanning compositions are products that color skin without
requiring full sun exposure, are contemplated within the sun care
category.
In yet another specific and non-limiting embodiment, the present
application provides a functional active selected from personal
care actives, cosmetic actives, nutraceutical actives or
pharmaceutical actives.
Accordingly, the functional active used in the present application
is present in an amount of about 1% wt./wt. to about 90% wt./wt. of
the total composition. Other non-limiting ranges for functional
actives include 1% to 5%, 5% to 10%, 10% to 15%, 15% to 20%, 20% to
25% or 25% to 30%, 30% to 40%, 40% to 50%, 50% to 60%, 60% to 70%,
70% to 80% and 80% to 90%.
In one non-limiting embodiment, the preferred functional active is
a sunscreen active containing UVA and/or UVB actives, organic or
mineral photo protective agents which is water-soluble,
lipo-soluble or insoluble in commonly known cosmetic solvents.
Non-limiting examples of UV actives include organic and inorganic
materials that scatter, absorb, and/or reflect radiation having a
wavelength from about 100 nm to about 400 nm. In one particular and
non-limiting aspect, the sun care composition protects UV-A, UV-B,
and/or UV-C radiation. UV-A radiation, from about 320 nm to about
400 nm, has the longest wavelengths within the UV spectrum, and
consequently is the least energetic. UV-A radiation includes UV-A1
(from about 340 nm to about 400 nm) and UV-A2 (from about 320 nm to
about 340 nm). UV-B radiation has shorter wavelengths, from about
290 nm to about 320 nm. UV-C radiation has the shortest wavelengths
from about 200 nm to about 290 nm. Suitable UV actives (or UV
filters) that can be selected for inclusion in the personal care
compositions most likely will depend on local regulations. It is
well known that commercially available sunscreens generally contain
combinations of multiple sunscreen actives.
Non-limiting examples of sunscreens (UV actives) useful in the
present application include octyl salicylate; p-aminobenzoic acid,
PEG-25PABA, Ethylhexyl dimethyl PABA, pentyl dimethyl PABA, octyl
dimethyl PABA, amyl dimethyl PABA, benzophenone-1, benzophenone-2,
benzophenone-3, benzophenone-4, benzophenone-5, benzophenone-6,
benzophenone-8, benzophenone-9,
2-(2H-benzotriazole-2-yl)-4,6-di-tert-pentylphenol,
ethyl-2-cyano-3,3-diphenyl acrylate, homo menthyl salicylate,
his-ethyl hexyloxyphenol methoxy phenyl triazine (bemotrizinol),
methyl-(1,2,2,6,6-pentamethyl-4-piperidyl)-sebacate,
2-(2H-benzotriazole-2-yl)-4-methylphenol, diethylhexyl butamido
triazone, 4,6-bis-(octylthiomethyl)-o-cresol,
Poly(4-hydroxy-2,2,6,6-tetramethyl-1-piperidine
ethanol-alt-1,4-butanedioic acid), red petroleum, octocrylene,
isoamyl-p-methoxycinnamate, drometrizole, drometrizole trisiloxane,
bisoctrizole,
2,4-di-tert-butyl-6-(5-chloro-2H-benzotriazole-2-yl)-phenol,
2-hydroxy-4-octyloxy benzophenone, diisopropyl methylcinnamate,
2-(1,1-dimethylethyl)-6-[[3-(1,1-demethylethyl)-2-hydroxy-5-methylphenyl]-
methyl-4-methylphenyl-acrylate, menthyl anthranilate, butyl methoxy
dibenzoyl methane, 2-ethoxyethyl p-methoxycinnamate, benzylidene
camphor sulfonic acid,
dimethoxyphenyl-[1-(3,4)]-4,4-dimethyl1,3-pentanedione,
N,N'-hexane-1,6-diylbis-[3-(3,5-di-tert-butyl-4-hydroxyphenyl-propionamid-
e)], pentaerythritol tetrakis
[3-(3,5-di-tert-butyl-4-hydroxyphenyl) propionate],
2,6-di-tert-butyl-4-[4,6-bis(octylthio)-1,3,5-triazin-2-ylamino]
phenol,
2-(2H-benzotriazole-2-yl)-4,6-bis(1-methyl-1-phenylethyl)phenol,
trolamine salicylate, diethylanolamine p-methoxycinnamate,
polysilicone-15, 4-methylbenzylidene camphor, n-phenyl-benzenamine,
reaction products with 2,4,4-trimethylpentene,
(2-ethylhexyl)-2-cyano-3,3-diphenylacrylate, digalloyl trioleate,
polyacrylamido methylbenzylidene camphor, glyceryl ethylhexanoate
dimethoxycinnamate,
1,3-bis-[(2'-cyano-3',3'-diphenylacryloyl)oxy]-2,2-bis-{[(2'-cyano-bis-(2-
,2,6,6-tetramethyl-4-piperidyl)-sebacate,
1,3,5-tris(3,5-di-tert-butyl-4-hydroxybenzyl)-1,3,5-triazine-2,4,6(1H,3H,
5H)-trione, hexamethylendiamine, ethyl-4-bis(hydroxypropyl)
aminobenzoate,
6-tert-butyl-2-(5-chloro-2H-benzotriazole-2-yl)-4-methyl phenol,
3,3',3'',5,5',5''-hexa-tert-butyl-.alpha.-.alpha.'-.alpha.''-(mes-
itylene-2,4,6-triyl) tri-p-cresol, ethylhexyl dimethoxybenzylidene
dioxoimidazoline propionate,
N,N'-bisformyl-N,N'-bis-(2,2,6,6-tetramethyl-4-piperidinyl),
3-benzylidene camphor, terephthalylidene dicamphor sulfonic acid,
camphor benzalkonium methosulfate, bisdisulizole disodium,
etocrylene, ferulic acid,
2-(2H-benzotriazole-2-yl)-4-(1,1,3,3-tetramethylbutyl)-phenol,
4,6-bis(dodecylthiomethyl)-o-cresol, .beta.-2-glucopyranoxy propyl
hydroxy benzophenone, phenylbenzimidazole sulfonic acid,
diethylamine hydroxy benzoyl hexylbenzoate,
3',3'-diphenylacryloyl)oxy]methyl}-propane, ethylhexyl
p-methoxycinnamate, avobenzone, camphor benzalkonium methosulfate,
phenylbenzimidazole sulfonic acid, terephthalidene dicamphor
sulfonic acid, benzylidene camphor sulfonic acid,
polyacrylamidomethyl benzylidene camphor, ethylhexyl
methoxycinnamate, ethylhexyl triazone, diethylhexyl butamido
triazone, 4-methylbenzylidene camphor, 3-benzylidene camphor,
methylene-bis-benztriazolyl tetramethylbutylphenol, disodium phenyl
dibenzimidazole tetrasulfonate, bisethylhexyloxyphenol
methoxyphenol triazine, polysilicone-15, 2,4,6-tris(Diisobutyl
4-aminobenzalmalonate)-s-triazine, inorganic sunscreen selected
from titanium dioxide and zinc oxide; micronized or unmicronized
mixtures thereof. As noted is contemplated that these actives can
be used in combinations.
Sunscreen actives (UV filters) used in present application may
include one or more of: Bemotrizinol (Escalol.TM. S UV filter
(Ashland)), Padimate 0 (Escalol.TM. 507 UV filter (Ashland)),
Avobenzone (Escalol.TM. 517 UV filter (Ashland)), Octinoxate
(Escalol.TM. 557 UV filter (Ashland)), Oxybenzone (Escalol.TM. 567
UV filter (Ashland)), Sulisobenzone (Escalol.TM. 577 UV filter
(Ashland)), Octisalate (Escalol.TM. 587 UV filter (Ashland)),
Homosalate (Escalol.TM. HMS UV filter (Ashland)), and Octocrylene
(Escalol.TM. 597 UV filter (Ashland)).
According to one particularly preferred and non-limiting
embodiment, the sunscreen active or agent is
bis-ethylhexyloxyphenol methoxyphenol triazine, marketed as
Escalol.RTM.S by Ashland Specialty Ingredients. The sunscreen
composition may additionally comprise at least one additional UV
filter and/or a mineral photo protective agent comprising treated
or untreated metal oxide pigments or nanopigments as part of the
desired composition. Applicants have found that the solubilizers
described herein find particular utility at solubilizing
bis-ethylhexyloxyphenol methoxyphenol triazine which is known to be
difficult to solubilize.
In another preferred embodiment, the present application discloses
a photo protective topical personal care composition, wherein the
composition is visibly transparent, free of odor and freeze thaw
stable.
According to one specific embodiment of the present application,
the composition is "visibly transparent" in that the composition is
able to be applied to a substrate and light is able to pass through
the composition with little or no distortion so that the substrate
can be clearly seen through the composition using the eye.
Transparency is measured using methods known to those skilled in
the art. In this specification, measurements of total absorbance
are used to demonstrate the level of transparency achieved using
various embodiments of the compositions being claimed.
According to another specific embodiment of the present
application, the present composition is "free of odor" in that the
sunscreen compositions comprising cyclohexyl toluate and
bemotrizinol when subjected to comparison studies with a panel of
odor evaluation experts were found to be acceptable. It has been
found that Cyclohexyl toluate has appreciable odor preference and
odor acceptance ratings over commercial solubilizer C12-15 alkyl
benzoate. Even after aging, low odor was observed.
In another specific embodiment, the present application further
comprises at least one adjuvant or additive or additional
ingredient selected from the group consisting of secondary polymers
for improving water-resistance, oils, waxes, solvents, emulsifiers,
preservatives, antioxidants, vitamins, perfumes, insect repellants,
dyes, pigments, fillers, film formers, buffers, spreading agents,
pearlizing agents, electrolytes, acids, bases, fatty substances,
organic solvents, ionic or nonionic, hydrophilic or lipophilic
thickeners, softeners, humectants, opacifiers, emollients,
fragrances, anionic surfactants, cationic surfactants, nonionic
surfactants, zwitterionic surfactants, amphoteric surfactants,
active agents, polymers, propellants, antioxidants, agents for
combating free radicals, alpha-hydroxy acids, moisturizing agents,
anti-inflammatory, colorants, pharmaceutically or dermatologically
or cosmetically acceptable excipients, skin care or hair care
agents, hair styling agents, hair fixative agents, structurants,
gelling agents, viscosity modifiers, electrolytes, pH adjusting
agents, organo silicones compounds, anti-dandruff agents,
antifoaming agents, anti-frizz agents, penetrants, conditioning
agents, chelating agents, antimicrobial agents, UV absorbers,
natural extracts, carriers, diluents, solvents, pharmaceutical
actives, lubricants, combing aids, plasticizers, solubilizers,
neutralizing agents, vapor pressure suppressants, bleaching agents,
hydrating agents, cosmetic adjuvants and/or additives, protectants,
and mixtures thereof.
Non-limiting examples of suitable antioxidants and/or antiradical
protecting agents include: BHA (tert-butyl-4-hydroxy anisole), BHT
(2,6-di-tert-butyl-p-cresol), TBHQ (tert-butyl hydroquinone),
proanthocyanodic oligomers, flavonoids, tetra amino piperidine,
erythorbic acid, spermine, cysteine, glutathione, superoxide
dismutase, lactoferrin and blends thereof.
Non-limiting examples of inorganic photo protective agents are
selected from pigments, preferably nanopigments (mean size of the
primary particles: generally from 5 nm to 10 nm, preferably from 1
nm to 5 nm) of treated or untreated metal oxides selected from
titanium oxide (amorphous or crystallized in rutile and/or anatase
form), iron oxide, zinc oxide, zirconium oxide or cerium oxide.
The additional photo protective agents are generally present in the
compositions according to the application in proportions ranging
from 0.01% wt./wt. to 70% wt./wt. of the total composition. Other
non-limiting ranges for additional photo protective agents include
0.01% to 1%, 1% to 5%, 5% to 10%, 10% to 15%, 15% to 20%, 20% to
25% or 25% to 30%, 30% to 40%, 40% to 50%, 50% to 60%, 60% to 70%
by weight of the total composition, and preferably ranging from
0.01% wt./wt. to 10% wt./wt. of the total composition.
Non-limiting examples of suitable preservatives include: benzoic
acid, sorbic acid, dehydroacetic acid, diazolidinyl ureas,
imidazolidinyl ureas, salicylic acid, piroctone olamine, DMDM
hydantoin, IPBC (iodopropynyl butylcarbamate), triclosan, bronopol,
formaldehyde, isothiazolinones, nitrates/nitrites, parabens,
phenoxyethanol, potassium sorbate, sodium benzoate, sulphites,
sulphur dioxide, and blends thereof. Preferred preservative include
methyl paraben, ethyl paraben, propyl paraben, phenoxy ethanol,
benzoic acid and dehydro acetic acid. Non-limiting ranges of
preservatives include 0.1% wt./wt. to 10% wt./wt. by weight of the
total composition. Other non-limiting ranges include 0.1% to 2%, 2%
to 4%, 4% to 6%, 6% to 8% or 8% to 10% by weight of the total
composition.
The physiological and cosmetically acceptable medium may consist
exclusively of water, a cosmetically acceptable solvent, or a blend
of water and a cosmetically acceptable solvent, such as a lower
alcohol composed of C.sub.1 to C.sub.4, such as ethanol,
isopropanol, t-butanol, n-butanol, alkylene glycols such as
propylene glycol, and glycol ethers. Preferred carrier or medium is
denatured alcohol, water, propylene glycol, ethanol,
trimethylamine, and glycerin. The carrier is present in amount of
about 2% wt./wt. to about 90% wt./wt. of the total topical
composition. Other non-limiting ranges for carrier include 5% to
10%, 10% to 15%, 15% to 20%, 20% to 25% or 25% to 30%, 30% to 40%,
40% to 50%, 50% to 60%, 60% to 70%, 70% to 80% and 80% to 90% by
weight of the total composition.
Non-limiting examples of suitable vitamins include: ascorbic acid
(vitamin C), vitamin E, vitamin E acetate, vitamin E phosphate, B
vitamins such as B3 and B5, niacin, vitamin A, derivatives thereof,
and blends thereof. Non-limiting ranges of vitamins include 0.1% to
10% by weight of the total composition. Other non-limiting ranges
include 0.1% to 2%, 2% to 4%, 4% to 6%, 6% to 8% or 8% to 10% by
weight of the total composition.
Non-limiting examples of surfactants include anionic surfactant,
cationic surfactant, non-ionic surfactant, amphoteric surfactant,
or zwitterionic surfactant. Non-limiting ranges of surfactants
include 0.1% wt./wt. to 10% wt./wt. of the total composition. Other
non-limiting ranges include 0.1% to 2%, 2% to 4%, 4% to 6%, 6% to
8% or 8% to 10% by weight of the total composition.
Non-limiting examples of anionic surfactants useful herein include
the water-soluble salts of alkyl sulfates having from 8 to 20
carbon atoms in the alkyl radical (e.g., sodium alkyl sulfate) and
the water-soluble salts of sulfonated monoglycerides of fatty acids
having from 8 to 20 carbon atoms selected from sarcosinates,
taurates, isethionates, sodium lauryl sulfoacetate, sodium laureth
carboxylate, and sodium dodecyl benzenesulfonate, sodium and
potassium salts of lauroyl sarcosinate, myristoyl sarcosinate,
palmitoyl sarcosinate, stearoyl sarcosinate, and oleoyl
sarcosinate. Preferred anionic surfactants are selected from sodium
lauryl sulfate (SLS) and sodium coconut monoglyceride
sulfonates.
Non-limiting examples of suitable cationic surfactants include:
derivatives of aliphatic quaternary ammonium compounds having at
least one long alkyl chain containing from about 8 to about 18
carbon atoms, such as, lauryl trimethylammonium chloride, cetyl
pyridinium chloride, cetyl trimethylammonium bromide, di-isobutyl
phenoxyethyl-dimethylbenzyl ammonium chloride, coconut
alkyltrimethylammonium nitrite, cetyl pyridinium fluoride, and
blends thereof. Further suitable are quaternary ammonium fluorides
having detergent properties such as compounds described in U.S.
Pat. No. 3,535,421. Certain cationic surfactants act as germicides
in the compositions disclosed herein.
Non-limiting examples of suitable nonionic surfactants include:
poloxamers (sold under the trade name Pluronic.RTM. by BASF
Corporation), polyethylene oxide condensates of alkyl phenols,
products derived from the condensation of ethylene oxide with the
reaction product of propylene oxide and ethylene diamine, ethylene
oxide condensates of aliphatic alcohols, long chain tertiary amine
oxides, long chain tertiary phosphine oxides, long chain dialkyl
sulfoxides, and blends thereof.
Non-limiting examples of suitable zwitterionic surfactants include
betaines and derivatives of aliphatic quaternary ammonium compounds
in which the aliphatic radicals can be straight chain or branched,
and which contain an anionic water-solubilizing group, e.g.,
carboxy, sulfonate, sulfate, phosphate, or phosphonate.
Non-limiting examples of suitable betaines include: decyl betaine
or 2-(N-decyl-N,N-dimethylammonio)acetate, coco betaine or
2-(N-coc-N,N-dimethyl ammonio)acetate, myristyl betaine, palmityl
betaine, lauryl betaine, cetyl betaine, stearyl betaine, and blends
thereof. The amidobetaines are exemplified by cocoamidoethyl
betaine, cocoamidopropyl betaine, lauramidopropyl betaine, and the
like. The betaines of choice include cocoamidopropyl betaines such
as lauramidopropyl betaine. Suitable betaine surfactants are
disclosed in U.S. Pat. No. 5,180,577.
Non-limiting examples of surfactants available commercially
include: (1) Alkanolamides, under the trade names Amidex.TM. and
Schercomid.TM.; amido-amines, under the trade names Katemul.TM. and
Schercodine.TM.; amine oxides, under the trade names Chemoxide.TM.
and Schercamox.TM.; amphoterics, under the trade names
Chembetaine.TM. Schercotaine.TM. and Schercoteric.TM.;
imidazolines, under the trade name Schercozoline.TM.; pearlizing
agents, under the trade name Quickpearl.TM.; performance
concentrates, under the trade names Sulfochem.TM. and Chemoryl.TM.;
soaps (potassium cocoate and potassium soyate); specialty
ethoxylates, under the trade name Chemonic.TM.; specialty quats
under the trade names Quatrex.TM. and Schercoquat.TM.; sulfates,
under the trade name Sulfochem.TM.; and sulfosuccinates, under the
trade name Chemccinate.TM. from Lubrizol. (2) Avaniel,
Cremaphore.RTM., Jordapan.RTM., and Pluracare.RTM. from BASF Corp.
(3) Miracare.RTM. SLB, Mackam.RTM. Bab, Mackanate.RTM. Ultra SI,
Miranol.RTM. Ultra, and Miracare.RTM. Plaisant from Rhodia. (4)
Stepan.RTM. Pearl 2, Stepan.RTM. Pearl 4, Stepan.RTM. Pearl Series,
Neobee.RTM. M-20, Stepan.RTM. PTC, Amphosol.RTM. 2CSF, Steol.RTM.,
Stepan-Mild.RTM. GCC, Stepan.RTM. SLL-FB, Stepanol.RTM. AM,
Stepanol.RTM. PB, Alpha-Step.RTM. BSS-45, Bio-Terge.RTM. 804,
Stepan-Mild.RTM. L3, Stepan.RTM. SLL-FB, Stepan.RTM. SSL-CG, and
Stepanol.RTM. CFAS-70 from Stepan Company.
Also suitable as surfactants are those described in the book
Surfactants in Personal Care Products and Decorative Cosmetics,
Third Edition, 2006, CRC Press. The disclosure is incorporated
hereby in its entirety by reference.
Non-limiting examples of skin conditioning agents include isodecyl
neopentanoate, Dicaprylyl carbonate, 2-ethylhexyl isononanoate,
Coco-caprylate Caprate, and Isodecyl Salicylate. Non-limiting
ranges of skin conditioning agents include 0.1% wt./wt. to 10%
wt./wt. of the total composition. Other non-limiting ranges include
0.1% to 2%, 2% to 4%, 4% to 6%, 6% to 8% or 8% to 10% by weight of
the total composition.
Non-limiting examples of lubricants useful for the present
application is selected from cyclopentasiloxane, diisopropyl
adipate, isocetyl alcohol. Non-limiting ranges of lubricants
include 0.1% wt./wt. to 10% wt./wt. of the total composition. Other
non-limiting ranges include 0.1% to 2%, 2% to 4%, 4% to 6%, 6% to
8% or 8% to 10% by weight of the total composition.
Non-limiting examples of emollient include lauryl lactate, C12-15
Alkyl lactate, methyl glucose sesquistearate and PEG-20 methyl
glucose sesquistearate. Non-limiting ranges of emollients include
0.1% wt./wt. to 10% wt./wt. by weight of the total composition.
Other non-limiting ranges include 0.1% to 2%, 2% to 4%, 4% to 6%,
6% to 8% or 8% to 10% by weight of the total composition.
Non-limiting examples of suitable silicones include polyalkyl
siloxanes, polyaryl siloxanes, polyalkyl aryl siloxanes, silicone
gums and resins, polyorgano siloxanes modified by organ functional
groups, and blends thereof. Preferred silicones include methicone,
caprylyl methicone, and cetyl dimethicone. Non-limiting ranges of
silicones include 0.1% wt./wt. to 10% wt./wt. of the total
composition. Other non-limiting ranges include 0.1% to 2%, 2% to
4%, 4% to 6%, 6% to 8% or 8% to 10% by weight of the total
composition.
Non-limiting examples of emulsifiers include ethoxylated fatty
acids, ethoxylated glyceryl esters, ethoxylated oils, ethoxylated
sorbitan esters, fatty esters, PEG esters and polyglycerol ester.
Preferred emulsifier is glyceryl stearate (and) laureth-23 (1%).
Non-limiting ranges of emulsifiers include 0.1% wt./wt. to 10%
wt./wt. of the total composition. Other non-limiting ranges include
0.1% to 2%, 2% to 4%, 4% to 6%, 6% to 8% or 8% to 10% by weight of
the total composition.
Non-limiting examples of buffering agents used in the present
application include alkali or alkali earth carbonates, phosphates,
bicarbonates, citrates, borates, acetates, acid anhydrides,
succinates and the like, such as sodium phosphate, citrate, borate,
acetate, bicarbonate, and carbonate. Non-limiting ranges of
buffering agents include 0.1% wt./wt. to 10% wt./wt. by weight of
the total composition. Other non-limiting ranges include 0.1% to
2%, 2% to 4%, 4% to 6%, 6% to 8% or 8% to 10% by weight of the
total composition.
Non-limiting examples of other additives used in the present
application include Ceteareth-20, Hydrogenated Polydecene (and)
Trideceth-6, cetyl alcohol, Caprylyl methicone for bringing about
desired feel and smoothness to the product.
Non-limiting examples of tanning or browning agents used in the
present application include dihydroxy acetone, satin, alloxan,
ninhydrin, glyceraldehyde, mesotartaric aldehyde, glutaraldehyde,
erythrulose, pyrazoline-4,5-dione derivatives, 4,4-dihydroxy
pyrazoline-5 and derivatives thereof. Non-limiting ranges of
tanning or browning agents include 0.1% wt./wt. to 10% wt./wt. by
weight of the total composition. Other non-limiting ranges include
0.1% to 2%, 2% to 4%, 4% to 6%, 6% to 8% or 8% to 10% by weight of
the total composition.
In another specific embodiment, the present application provides a
photo protective topical composition formulated into an
oil-in-water emulsion, a water-in-oil emulsion, an oil-water-oil
emulsion, a water-oil-water emulsion, a water-in-silicone emulsion,
an oily solution, a lipid fusion, a hydro-alcoholic gel, an
anhydrous formulation, an anhydrous spray, an anhydrous gel, an
anhydrous dry gel, an aqueous gel, a gel cream SPF 20, a SPF 30
cream, an alcoholic solution, a hydro-alcoholic solution, a milk, a
lotion, a powder, a stick, a roll-on, a mist, a wipe, wax, a
mousse, an aerosol, a balm, a patch, a pomade, a pump spray, a
solution, a towelette, paste, powder or a spray.
Non-limiting examples of skin care formulation in the present
application include: solutions, oils, lotions, creams, ointments,
liquids, gels, solids, W/O emulsions, O/W emulsions, milks,
suspensions, micro emulsions, dispersions, microencapsulated
products, sticks, balms, tonics, pastes, mists, reconstitutable
products, peels, soaps, aerosols, mousses, waxes, glues, pomades,
spritzes, putties, lacquers, serums, perms, powders, pencils,
flakes, blush, highlighters, bronzers, concealers, and 2-way cake
products. The compositions of the application include skin-washing
compositions, particularly in the form of solutions or gels for the
bath or shower, or make-up removal products.
The six product categories provided below are included under subset
of skin care.
Eye Care--Non-limiting eye care product forms include: mascaras,
eye liners, eye shadows, curlers of eye lashes, eyebrow pencils,
and eye pencils.
Lip Care--Non-limiting lip care product forms include: lipsticks,
lip balms, lip pencils, lip glosses, lip sprays, transparent lip
bases, tinted lip moisturizers, and multi-functional color sticks
that can also be used for cheeks and eyes.
Nail Care--Non-limiting nail care product forms include: nail
polishes, nail varnishes, enamels, nail varnish removers,
home-manicure products such as cuticle softeners and nail
strengtheners, and artificial nails.
Face Care--Non-limiting face care product forms include: creams,
lotions, solutions, oils, liquids, peels, scrubs, emulsions,
suspensions, micro emulsions, microencapsulated product, pastes,
reconstitutable product, aerosols, mousses, gels, waxes, glues,
pomades, spritzes, facial wet-wipes, putties, lacquers, serums,
perms, powders, blush, highlighters, bronzers, masks, and
concealers.
Body Care--Non-limiting body care product forms include: foams,
peels, masks, gels, sticks, aerosols, lotions, salts, oils, balls,
liquids, powders, peels, pearls, bar soaps, liquid soaps, body
washes, cleansers, scrubs, creams, flakes, other bath and shower
products, shaving products, waxing products, and sanitizers.
Foot Care--Non-limiting foot care product forms include: mousses,
creams, lotions, powders, liquids, sprays, aerosols, gels, flakes,
and scrubs.
The present photo protective composition is capable of protecting
human skin against the harmful effects of irradiation of sun.
It is also contemplated that the personal care compositions are
used in products for male and/or female personal grooming and/or
toiletry selected from sanitary napkins, baby diapers, adult
diapers, feminine products, products for incontinence, and other
related products.
In yet another specific embodiment, the present application
provides a photo protective topical sunscreen composition for the
UV-photo protection of human skin and/or hair comprising: (a) about
1% wt./wt. to about 70% wt./wt. of at least one active sunscreen
agent; (b) about 0.1% wt./wt. to about 50% wt./wt. of at least one
solubilizing compound selected from cyclohexyl 3-toluate,
cyclohexyl 4-toluate or combination thereof; and (c) about 1%
wt./wt. to about 80% wt./wt. of at least one topically applicable,
cosmetically or dermatologically acceptable carrier.
The present sunscreen composition may further comprise polymers for
enhanced performance and feel for the sunscreen compositions
selected from .alpha.-olefin/Poly vinyl pyrrolidone (Ganex line
from Ashland Specialty Ingredients) and Vinyl Acetate: Mono-n-butyl
Maleate: Isobornyl acrylate (Advantage-Plus line from Ashland
Specialty Ingredients). Addition of these polymers shows increased
critical wavelength and UVA/UVB absorbance ratio.
In yet another specific embodiment, the present application
provides a method for cosmetically treating or caring for the skin,
lips, nails, hair, ears, eyelashes, eyebrows and/or scalp
comprising topically applying thereon, an effective amount of the
photo protective topical composition comprising (i) at least one
functional active; and (ii) at least one solubilizing compound
having the formula I:
##STR00005## wherein R is C.sub.5-C.sub.10 cycloalkyl or linear or
branched alkylcycloalkyl, wherein the ring size is C.sub.5-C.sub.7;
R.sub.1, R.sub.2, and R.sub.3 are each independently selected from
the group consisting of H, and linear or branched C.sub.1-C.sub.4
alkyl, provided that at least two of R.sub.1, R.sub.2, R.sub.3 are
H; wherein said solubilizing compound is present in an amount
effective to solubilize said functional active.
In yet another specific embodiment, the present application
provides a method for photo protecting the exposed and/or unexposed
skin, nails, hair, lips, ears, eyebrows, eyelashes, and/or scalp,
against the damaging effects of UV-irradiation comprising topically
applying thereon, an effective amount of the
cosmetic/dermatological composition comprising: (i) at least one
functional active; and (ii) at least one solubilizing compound
having the formula I
##STR00006## wherein R is C.sub.5-C.sub.10 cycloalkyl or linear or
branched alkylcycloalkyl, wherein the ring size is C.sub.5-C.sub.7;
R.sub.1, R.sub.2, and R.sub.3 are each independently selected from
the group consisting of H, and linear or branched C.sub.1-C.sub.4
alkyl, provided that at least two of R.sub.1, R.sub.2, R.sub.3 are
H; wherein said solubilizing compound is present in an amount
effective to solubilize said functional active.
In order to further illustrate the present application and the
advantages thereof, the following specific examples are given, it
being understood that same are intended only as illustrative and by
no means limitative. In said examples to follow, all parts and
percentages are given by weight, unless otherwise indicated.
Example 1: Synthesis of Cyclohexyl 3-Toluate
Cyclohexyl 3-Toluate was prepared by reacting Cyclohexyl alcohol
and 3-Toluic acid in the presence of a catalyst, e.g., a Lewis acid
and/or organic/inorganic catalyst.
##STR00007##
A dry 2-L, 4-neck round bottom flask, fitted with a mechanical
stirrer, heating mantle/temperature controller/thermocouple,
Dean-Stark trap with reflux condenser and charging port was charged
with 601.0 g (6.0 mol) of warm cyclohexanol at 50-80.degree. C. and
mixed with 3.3 g of Lewis acid catalyst. The content of the flask
was heated to 80-110.degree. C. and 680.8 g (5.0 mol) of 3-Toluic
acid was added to the flask with a stirring. The reaction mixture
was heated to 230-232.degree. C. and the reaction water was
removed. The final reaction mixture with acid number .ltoreq.1 mg
KOH/g was distilled under vacuum. Yield of Cyclohexyl 3-Toluate:
93%. Purity: 99.6%. Solubility of Escalol S at 25.degree. C.: 35%
& Solubility of Avobenzone at 25.degree. C.: 26%
Example 2: Synthesis of Cyclohexyl 4-Toluate
Cyclohexyl 4-Toluate was prepared by reacting Cyclohexyl alcohol
and 4-Toluic acid in the presence of a catalyst, e.g., a Lewis acid
and/or organic/inorganic catalyst.
##STR00008##
The reaction was run as described above. The flask was charged with
601.0 g (6.0 mol) of warm Cyclohexanol, 3.3 g of Lewis acid
catalyst and 680.8 g (5.0 mol) of 4-Toluic acid. The reaction
mixture was heated to 230-232.degree. C. and the reaction water was
removed. The final reaction mixture with acid number 1.1 mg KOH/g
was distilled under vacuum. Yield of Cyclohexyl 4-Toluate: 90%.
Purity: 99.7%. Solubility of Escalol S at 25.degree. C.: 36% &
Solubility of Avobenzone at 25.degree. C.: 26%
Example 3: Synthesis of Cyclohexyl 2-Toluate
Cyclohexyl 2-Toluate was prepared by reacting Cyclohexyl alcohol
and 2-Toluic acid in the presence of a catalyst, e.g., a Lewis acid
and/or organic/inorganic catalyst. A dry 1-L, 4-neck round bottom
flask, fitted with a mechanical stirrer, heating mantle/temperature
controller/thermocouple, Dean-Stark trap with reflux condenser and
charging port was charged with 300.5 g (3.0 mol) of Cyclohexanol,
1.6 g of Lewis acid catalyst and 340.4 g (2.5 mol) of 2-Toluic
acid. The reaction mixture was heated to 230-232.degree. C. and the
reaction water was removed. The final reaction mixture with acid
number 3.6 mg KOH/g was distilled under vacuum. Yield of Cyclohexyl
2-Toluate: 94%. Purity 99.4%; Solubility of Escalol S at 25.degree.
C.: 37%; Solubility of Avobenzone at 25.degree. C.: 23%
##STR00009##
Example 4: Synthesis of Cyclohexyl Toluate (Mixture of Cyclohexyl
3-Toluate and Cyclohexyl 4-Toluate)
Cyclohexyl Toluate mixture was prepared by reacting Cyclohexyl
alcohol and the mixture of 3-Toluic acid and 4-Toluic acid in the
presence of a catalyst, e.g., a Lewis acid and/or organic/inorganic
catalyst.
##STR00010##
The reaction was run as described above. The flask was charged with
601.0 g (6.0 mol) of warm cyclohexanol, 3.3 g of Lewis acid
catalyst and 680.8 g (5.0 mol) of the mixture of 3-Toluic acid with
4-Toluic acid. The reaction mixture was heated to 230-232.degree.
C. and the reaction water was removed. The final reaction mixture
with acid number <1 mg KOH/g was distilled under vacuum. Yield
of Cyclohexyl Toluate: 94%. Purity: 99.8%. Solubility of Escalol S
at 25.degree. C.: 36% & Solubility of Avobenzone at 25.degree.
C.: 25%
Example 5: Synthesis of Cyclohexylmethanol 3-Toluate
Cyclohexylmethanol 3-Toluate was prepared by reacting
Cyclohexylmethanol with 3-Toluic acid in the presence of a
catalyst, e.g., a Lewis acid and/or organic/inorganic catalyst.
##STR00011##
The reaction was run as described above. The flask was charged with
452.2 g (3.96 mol) of cyclohexylmethanol, 2.3 g of Lewis acid
catalyst and 449.3 g (3.3 mol) of 3-Toluic acid. The reaction
mixture was heated to 230.degree. C. and the reaction water was
removed. The final reaction mixture with acid number <1 mg KOH/g
was distilled under vacuum. Yield of cyclohexylmethanol 3-Toluate:
93.4%. Purity: 99.6%. Solubility of Escalol S at 25.degree. C.: 30%
& Solubility of Avobenzone at 25.degree. C.: 25%
Example 6: Synthesis of Cyclopentyl 3-Toluate
Cyclopentyl 3-Toluate solubilizer was prepared by reacting
Cyclopentyl alcohol with 3-Toluic acid in the presence of a
catalyst, e.g., a Lewis acid and/or organic/inorganic catalyst.
##STR00012##
The reaction was run as described above. The flask was charged with
375.0 g (4.4 mol) of Cyclopentyl alcohol, 2.5 g of Lewis acid
catalyst and 544.6 g (4.0 mol) of 3-Toluic acid. The reaction
mixture was heated to 220.degree. C. and the reaction water was
removed. The final reaction mixture with acid number 4.5 mg KOH/g
was distilled under vacuum. Yield of Cyclopentyl 3-Toluate: 92%.
Purity 99.5%; Solubility of Escalol S at 25.degree. C.: 34%;
Solubility of Avobenzone at 25.degree. C.: 28%
Physical properties of the synthesized cycloalkyl aryl esters are
disclosed in Table 1, where the physical properties include acid
number, American Public Health Association [APHA] color, refractive
index and specific gravity.
TABLE-US-00001 TABLE 1 Properties of the synthesized cycloalkyl
aryl esters Acid APHA Refractive Specific Compound number color
Index Gravity Cyclohexyl 3-Toluate 0.1 5.3 1.5187 1.0381 Cyclohexyl
4-Toluate 0.1 8.0 1.5199 1.0352 Cyclohexyl 2-Toluate 1.4 15.7
1.5214 1.0459 Cyclohexyl Toluate 0.1 2.6 1.5198 1.0361 (mixture of
isomers) Cyclohexylmethanol 3- 0.1 <1 1.5168 1.0276 Toluate
Cyclopentyl 3-Toluate 3.5 8.9 1.5195 1.0493
Example 7: Solubility of Various Sunscreens in Different
Solubilizing Media
TABLE-US-00002 TABLE 2 Solubility of sunscreen actives Solubility @
25.degree. C. Compound Escalol S Avobenzone Oxybenzone Cyclohexyl
2-Toluate 37 23 32 Cyclohexyl 3-Toluate 35 26 33 Cyclohexyl
4-Toluate 36 26 32 Cyclohexyl Toluate (mixture 36 25 32 of
Cyclohexyl 3-Toluate and Cyclohexyl 4-Toluate) Cyclohexylmethanol
3- 30 25 33 Toluate Cyclopentyl m-Toluate 34 28 39 Phenethyl
benzoate 22 20 34 C12-15 alkyl benzoate 13 12 15
The sunscreens show increased solubility where cyclohexyl compounds
were used as demonstrated in Table 2. Escalol.RTM.S showed more
than a 1.5-fold increase in solubility in the compounds of this
application compared with X-Tend 226, which is a solubilizer for
sunscreen actives in widespread commercial use.
Example 8: Comparison Studies of Sunscreens with Cycloalkyl Toluate
and Other Solubilizing Compounds
Different samples of the current solubilizing compound cycloalkyl
toluate was combined with available sunscreens Escalol S,
avobenzone and oxybenzone at 25.degree. C. The tests show clear
solution whereas samples with commercial sunscreen solubilizers
X-Tend.RTM. 226 and Finsolv.RTM. TN show crystal formations. The
results are shown in FIG. 6. Solubility was checked for cyclohexyl
ester in various sunscreen actives such as bemotrizinol, ethylhexyl
triazone, avobenzone & benzophenone-3 in comparison to
phenethyl benzoate. It was observed that cyclohexyl ester was best
solubilizer for Bemotrizinole, avobenzone and benzophenone-3 over
phenethyl benzoate, the results are provided in FIG. 2. Sunscreen
active comprising cyclohexyl toluate as solubilizer shows increased
solubility percentages of about 22% to about 33%, compared to
sunscreen active comprising C12-15 alkyl benzoates as solubilizers
which showed around 4% to around 15% of solubility, the results are
depicted in FIG. 3. Similar results are observed when sunscreen
actives are screened for other esters as solubilizers selected from
phenethyl benzoate, diisopropyl adipate, C12-15 lactate, ethylhexyl
palmitate, dicaprylyl carbonate, C12-15 alkyl benzoate (and)
dipropylene glycol dibenzoate (and) PPG 15 stearyl ether benzoate,
dipropylene glycol dibenzoate and compared with sunscreen
comprising cyclohexyl toluate, results are shown in FIG. 4 &
FIG. 5.
Example 9: Expert Odor Evaluations
TABLE-US-00003 Cyclohexyl Toluate Bemotrizinol Fresh Aged Product
Chasis % w/w level % w/w Sample Sample SPF 30 O/W 5.00 1.00
Accepted Accepted Cream cream SPF 20 O/W 5.00 3.00 Accepted
Accepted Cream cream Spray Anhy- 3.00 2.00 Accepted Accepted
drous
Sunscreen having cyclohexyl toluate and bemotrizinol as
solubilizers were tested for odor by an expert panel of 12 members
and appreciable level of odor acceptance results were reported.
Odor acceptance and odor preference values are shown in FIG. 1.
Example 10--Formulation--Comparison of Solubility
TABLE-US-00004 Sample A Sample B Ingredient Name % w/w % w/w Phase
A Alcohol Denatured 51.00 51.00 Phase B Butyl Methoxy dibenzoyl
3.00 3.00 methane (Avobenzone) Octisalate 5.00 5.00
Bis-ethylhexyloxyphenol 3.00 3.00 methoxy phenyl triazine
(Bemotrizinol) Homosalate 10.00 10.00 Ethylhexyl triazone 3.00 3.00
Isodecyl neopentanoate 10.00 10.00 Diisopropyl adipate 5.00 5.00
C12-15 Alkyl Benzoate -- 10.00 Cyclohexyl toluate 10.00 -- Total
100.00 100.00
Sample A had cyclohexyl toluate as solubilizer and Sample B had
C12-15 alkyl benzoate. When two samples were tested for solubility,
it showed that no crystals were formed in Sample A whereas Sample B
showed crystals. The results are depicted in FIG. 1.
Example 11--Formulation--Anhydrous Spray
TABLE-US-00005 Sample C Ingredient Name % w/w Phase A Alcohol
Denatured 40.25 Vinyl Acetate/Butyl 2.00 Maleate/Isobornyl Acrylate
copolymer Phase B Butyl 3.00 Methoxydibenzoylmethane
Bis-ethylhexyloxyphenol 2.00 methoxy phenyl triazine (Bemotrizinol)
Octisalate 5.00 Homosalate 10.00 Octocrylene 8.00 Isocetyl alcohol
5.00 Dicaprylyl carbonate 5.25 2-ethylhexyl isononanoate 5.50 Phase
C Caprylyl methicone 7.00 Cyclopentasiloxane 2.00 Cyclohexyl
toluate 5.00 Total 100.00
An anhydrous spray was prepared using cyclohexyl toluate (5%). A
clear yellow liquid was obtained.
Example 12--Formulation--Anhydrous Spray
TABLE-US-00006 Sample D Ingredient Name % w/w Phase A Alcohol
Denatured 42.25 VA/Butyl Maleate/Isobornyl 2.00 Acrylate copolymer
Phase B Butyl Methoxydibenzoylmethane 3.00 Bis-ethylhexyloxyphenol
methoxy 3.00 phenyl triazine (Bemotrizinol) Octisalate 5.00
Homosalate 10.00 Octocrylene 5.00 Isocetyl alcohol 5.00
Coco-caprylate Caprate 5.25 2-ethylhexyl isononanoate 5.50 Phase C
Caprylyl methicone 7.00 Cyclopentasiloxane 2.00 Cyclohexyl toluate
5.00 Total 100.00
An anhydrous spray was prepared using cyclohexyl toluate (5%). A
clear yellow liquid was obtained.
Example 13--Formulation--Anhydrous Spray
TABLE-US-00007 Sample E Ingredient Name % w/w Phase A Ethanol 44.00
VA/Butyl Maleate/Isobornyl 2.00 Acrylate copolymer Phase B Butyl
Methoxydibenzoylmethane 3.00 (Avobenzone) Octisalate 5.00
Homosalate 10.00 Octocrylene 8.00 Bis-ethylhexyloxyphenol methoxy
2.00 phenyl triazine (Bemotrizinol) Cyclohexyl Toluate 3.00
Diisopropyl Adipate 5.00 Lauryl Lactate 5.00 C12-15 Alkyl lactate
5.00 Dicaprylyl carbonate 4.00 Isodecyl Salicylate 3.00 Total
100.00
An anhydrous spray was prepared using cyclohexyl toluate (3%). A
clear yellow liquid was obtained.
Example 14--Formulation--Anhydrous Dry Gel
TABLE-US-00008 Sample F Ingredient Name % w/w Phase A Butyl Methoxy
dibenzoylmethane 3.00 Bis-Ethylhexyloxyphenol methoxy 2.00 phenyl
triazine Ethylhexyl Salicylate 5.00 Homosalate 10.00 Octocrylene
8.00 Cyclohexyl Toluate 5.00 Phase B Diisopropyl Adipate 7.00
Isocetyl Alcohol 2.50 Lauryl Lactate 6.50 Isodecyl Neopentanoate
1.00 Ethylhexyl Isononanoate 2.00 Phase C Acrylates/C12-22 Alkyl
1.00 Methacrylate Copolymer (and) Water/Aqua (and) Propylene glycol
PolyVinylPyrrolidone 4.00 Alcohol Denatured 43.00 Total 100.00
An anhydrous dry gel was prepared using cyclohexyl toluate (5%).
Viscosity (D1): 30000-35000 cps as measured by (Brookfield RVT/T
C/5 rpm/25 C/1 min)
Example 15--Formulation--Gel Cream SPF 20
TABLE-US-00009 Sample G Ingredient Name % w/w Phase A Water 61.78
Glycerin 2.00 Propylene Glycol 3.00 Triethanolamine 0.05 Acrylic
acid/Vinyl Pyrrolidone 0.30 crosspolymer Phenoxyethanol (and)
Methyl paraben 1.00 (and) Ethyl paraben (and) Propylparaben Phase B
Homosalate 10.00 Octocrylene 5.00 Butyl methoxydibenzoyl methane
3.00 Bis-Ethylhexyloxyphenol 3.00 Methoxyphenyl triazine Glyceryl
Stearate (and) Laureth-23 1.00 Ceteareth-20 0.50 Cyclohexyl Toluate
5.00 Phase C Triethanolamine 0.70 Phase D Sodium Polyacrylate (and)
0.30 Hydrogenated Polydecene (and) Trideceth-6 Phase E Ethylhexyl
isononanoate (and) Cetyl 1.00 Dimethicone Dimethicone/Vinyl
Dimethicone 3.00 Crosspolymer (and) Isododecane Total 100.00
A gel cream was prepared using cyclohexyl toluate (5%). Viscosity
(D1): 27,000-33,000 cps as measured by (Brookfield RVT/TB/5 rpm/25
C/1 min) and pH at 5.75-6.25
Example 16--Formulation--SPF 20 Cream
TABLE-US-00010 Sample H Ingredient Name % w/w Phase A Water 62.50
Glycerin 3.00 Disodium Ethylene Diamine Tetra 0.10 Acetic acid
(EDTA) Triethanolamine 0.50 Acrylic acid/VP Crosspolymer 0.70 Phase
B Dimethicone 0.50 PEG-20 Methyl Glucose 2.50 Sesquistearate Methyl
Glucose Sesquistearate 0.50 Cetyl Alcohol 1.50 Isodecyl
neopentanoate 3.00 Butyl methoxydibezoylmethane 1.00 (Avobenzoen)
Octisalate 5.00 Octocrylene 2.00 Bis-Ethylhexyloxyphenol 3.00
Methoxyphenyl Triazine (Bemotrizinol) Cyclohexyl Toluate 5.00 Phase
C Cyclopentasiloxane 5.00 Cyclopentasiloxane (and) 1.00
Dimethicone/Vinyltrimethylsiloxysilicate Crosspolymer Phase D
Phenoxyethanol (and) benzoic 0.75 Acid (and) Dehydroacetic Acid
Total 100.00
SPF 20 cream was prepared using cyclohexyl toluate (5%). Viscosity:
9000-1000 cps was observed as measured by (Brookfield RVT/TB/10
rpm/25 C/1 min) at pH: 5.30-5.70
Example 17--Formulation--SPF 30 Cream
TABLE-US-00011 Sample I Ingredient Name % w/w Phase A Water 62.15
Carbomer 0.40 Phase B Avobenzone 1.00 Octisalate 5.00 Homosalate
10.00 Octocrylene 0.80 Benzopheneone-3 4.00 Bemotrizinol 1.00
Glyceryl Stearate (and) Laureth-23 3.00 Ceteareth-20 1.50
Cyclohexyl Toluate 5.00 Phase C Water 5.00 Triethanolamine 0.40
Phase D Propylene Glycol (and) 0.75 Diazolidinyl Urea (and)
Methylparaben (and) Propylparaben Total 100.00
SPF 30 cream was prepared using cyclohexyl toluate (5%). Viscosity:
30000-35000 cps was observed as measured by (Brookfield RVT/TB/10
rpm/25 C/1 min) at pH: 6.00-6.50.
While this invention has been described in detail with reference to
certain preferred embodiments, it should be appreciated that the
present invention is not limited to those precise embodiments.
Rather, in view of the present disclosure, which describes the
current best mode for practicing the invention, many modifications
and variations would present themselves to those skilled in the art
without departing from the scope and spirit of this invention.
* * * * *